1-benzyl-2,3-dihydroindole-5-carbaldehyde → 5-Methylindoline

HRID 1108477Notes

Reaction equation

HRID 1108477 reaction equation
C([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH:17]=O)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[CH3:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[NH:8][CH2:9][CH2:10]2

Participants

5

Reactant 2

HCID 9275671-benzyl-2,3-dihydroindole-5-carbaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 140236795-MethylindolineYield 80.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Into a 200 mλ atmospheric pressure hydrogenation apparatus equipped with a thermometer and a stirrer, 2.0 g (0.0084 mol) of 1-benzyl-5-formylindoline, 0.4 g of 5% 5 Pd/C and 100 mλ of ethanol were charged, and while introducing hydrogen under atmospheric pressure, a reaction was carried out at from 60 to 70° C. for 8 hours, and when the absorption of hydrogen ceased, the reaction was terminated. After termination of the reaction, the lo palladium catalyst (5% Pd/C) was collected by filtration, and ethanol was distilled off under reduced pressure to obtain a slightly red liquid. The obtained liquid was subjected to vacuum distillation to obtain 0.9 g of 5-methylindoline having a boiling point of 93° C./4 mmHg. The yield was 80.4% (based on the 1-benzyl-5-formylindoline).

Workup

  1. additionwere charged
  2. customwhen the absorption of hydrogen
  3. customthe reaction was terminated
  4. customAfter termination of the reaction
  5. filtrationthe lo palladium catalyst (5% Pd/C) was collected by filtration, and ethanol
  6. distillationwas distilled off under reduced pressure
  7. customto obtain a slightly red liquid
  8. distillationThe obtained liquid was subjected to vacuum distillation

Sources & evidence

ORD record
ord-fe2d1e3a362d4652b66c40faa6b31731
Source dataset
uspto-grants-2000_05
Patent number
US06066744

Reaction notes

Loading…